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Check prices for these dates

Next weekend
7 Rab. I - 9 Rab. I
In two weeks
14 Rab. I - 16 Rab. I
In one month
28 Rab. I - 30 Rab. I
In two months
25 Rab. II - 27 Rab. II

Compare Villas in Winter Garden with updated reviews, rates, and availability.

Lakeview Luxury Villa with Everything
Pool

Lakeview Luxury Villa with Everything

9.8 out of 10, Exceptional, (325)
"This place was amazing and everything we would want for 6 adults and 4 kids ages 4-8. Close to Disney. Property manager was great in responding to the little things that weren’t quite right. We would stay here again. "
Lakeview Luxury Villa with Everything
Modern Luxury Villa with Everything
Pool

Modern Luxury Villa with Everything

9.8 out of 10, Exceptional, (374)
"Just as advertised, lots of parking , great place. The audio Video was not hooked up right was the only complaint other than that would book again!"
Modern Luxury Villa with Everything
Lakeview Luxury Villa with Everything
Pool

Lakeview Luxury Villa with Everything

10.0 out of 10, Exceptional, (73)
"Love the property! Great hosts, house and location! "
Lakeview Luxury Villa with Everything
Ultimate Lakeview Villa with Everything!
Pool

Ultimate Lakeview Villa with Everything!

9.4 out of 10, Exceptional, (98)
"The house was awesome, looked like the photos! Clubhouse was also fun!We even saw an alligator in the pond! "
Ultimate Lakeview Villa with Everything!
Heavenly 5 Bedroom, 6 Bathroom Private Pool Home with Beautiful Lakeview in Gated Resort!
Interior

Heavenly 5 Bedroom, 6 Bathroom Private Pool Home with Beautiful Lakeview in Gated Resort!

9.2 out of 10, Wonderful, (10)
"The house is beautiful, biggest, confortable. We lover and our children too. So near to a walmart and to disney. Fully recomended"
Heavenly 5 Bedroom, 6 Bathroom Private Pool Home with Beautiful Lakeview in Gated Resort!
Large Margaritaville Villa w/ Private Pool + View
Miscellaneous

Large Margaritaville Villa w/ Private Pool + View

4.0 star property
8.4 out of 10, Very Good, (5)
"Great property, comfortable beds, kitchen equipped with everything you need, washer and dryer, dinning table for 10 people, every room with tv, terrace tv, bathroom and small pool but very pleasant. No rooms on first floor. 3 rooms on second floor and 2 rooms on third floor. I will stay again."
Large Margaritaville Villa w/ Private Pool + View
*Nice Greenbackyard*Cozy 6BR Windsor Hills Pool Villa,2 Miles To Disney
Outdoor pool, a heated pool

*Nice Greenbackyard*Cozy 6BR Windsor Hills Pool Villa,2 Miles To Disney

9.2 out of 10, Wonderful, (63)
"Property is quite spacious and ideally located close to Disney. The gated community adds an additional layer of security that makes it great for families. Owner was very communicative and provided great details on accessing the property and as well very responsive to questions or issues. Will definitely stay here again on our next trip. "
*Nice Greenbackyard*Cozy 6BR Windsor Hills Pool Villa,2 Miles To Disney
Beautiful Spacious 3 Bedroom Villa with Private Pool and Wonderful Lake View
Pool

Beautiful Spacious 3 Bedroom Villa with Private Pool and Wonderful Lake View

8.6 out of 10, Excellent, (83)
"We have stayed at this property 3 times. The host is amazing, very responsive and kind. The location is great and the home is a great value. "
Beautiful Spacious 3 Bedroom Villa with Private Pool and Wonderful Lake View
Ultimate Lakeview Villa with Everything!
Pool

Ultimate Lakeview Villa with Everything!

9.8 out of 10, Exceptional, (336)
"Dope crib, Huge "
Ultimate Lakeview Villa with Everything!
Villa in Kissimmee next to Disney!
Pool

Villa in Kissimmee next to Disney!

8.0 out of 10, Very Good, (16)
"Nothing really to complain about, a little dusty and could use a deep cleaning for the carpets"
Villa in Kissimmee next to Disney!
Modern Luxury Villa with Everything
Pool

Modern Luxury Villa with Everything

9.6 out of 10, Exceptional, (211)
"Our entire family from old to young enjoyed this vacation home. We weren’t far at all to all Disney parks. Lots of restaurants and shopping options near the home. Very quiet area to be able to rest and relax in between park visits. Communication was very simple and easy also. If we go back to Disney, we will be back to this property for sure!"
Modern Luxury Villa with Everything
Modern villa with patio, grill, central AC, WiFi, shared pool, tennis, & gym
Lobby

Modern villa with patio, grill, central AC, WiFi, shared pool, tennis, & gym

9.6 out of 10, Exceptional, (7)
"We would return again"
Modern villa with patio, grill, central AC, WiFi, shared pool, tennis, & gym
Champions Gate Luxury 6 Bedroom Resort Villa With Spa and Games Room on Golf Course community
A heated pool

Champions Gate Luxury 6 Bedroom Resort Villa With Spa and Games Room on Golf Course community

8.6 out of 10, Excellent, (33)
"Lovely villa, excellent area to stay, we loved the club house and all the amenities. Would definitely stay again. Any problems we had were sorted quickly, excellent service. "
Champions Gate Luxury 6 Bedroom Resort Villa With Spa and Games Room on Golf Course community
Outstanding 6 Bed Villa, Pool & Spa, Superb Lakefront Setting, 5* Windsor Hills
Outdoor pool, a heated pool

Outstanding 6 Bed Villa, Pool & Spa, Superb Lakefront Setting, 5* Windsor Hills

10.0 out of 10, Exceptional, (169)
"The home and location were just as stated on line. We paid extra for the pool to heated during our stay and it was perfect. The home is within easy access to shopping, groceries, restaurants, and theme parks. The home had lots of glasses, dishes, and cutlery. The downside to our trip was it there was not enough essentials in the home. There was 6 adults and 3 children in our group and we stayed for 9 days. We only had the 1 roll of toilet paper that was on the dispenser in each bathroom,...
Outstanding 6 Bed Villa, Pool & Spa, Superb Lakefront Setting, 5* Windsor Hills
Experience Kissimmee living near vibrant Old Town
Exterior

Experience Kissimmee living near vibrant Old Town

9.4 out of 10, Exceptional, (29)
"Basically nice and convenient property. Jump to the cons: dated, ceiling fan in living room absolutely filthy. Two story house with 1 thermostat, upstairs hot and lower level cold. Ordered pool heated and couldn't get water above 70⁰ ( note: it was unusually cold during our stay. Owner was very responsive and refunded heating fees in full.) Even with just a 2 night stay we ran out of toilet paper. There wasn't even half a roll in each bathroom.We were only there for 2 nights before a cruise so...
Experience Kissimmee living near vibrant Old Town
Private Heated Pool! Only 8 miles to Disney! Gated Community
Outdoor pool, a heated pool

Private Heated Pool! Only 8 miles to Disney! Gated Community

10.0 out of 10, Exceptional, (51)
"Clean, quiet, close to Disney, great communication and easy check in and out procedures. Everything was perfect and smooth. Would definitely stay here again. "
Private Heated Pool! Only 8 miles to Disney! Gated Community
Beautiful 12 bedroom 11 Bathroom house Bella Vida Resort Villa
Fridge, microwave, oven, stovetop

Beautiful 12 bedroom 11 Bathroom house Bella Vida Resort Villa

8.6 out of 10, Excellent, (4)
"The house was great and fit our needs very well. Large kitchen with 2 refrigerators and 2 dishwashers, as well as well-stocked cupboards with dishes. The dining and living room area was comfortable for all of us. The game room was wonderful for the kids and we all enjoyed the pool and hot tub. Located close to many parks and shopping areas. We enjoyed the house very much! "
Beautiful 12 bedroom 11 Bathroom house Bella Vida Resort Villa
4 Bedroom Villa 2 Miles from Disney Entrance Kissimmee Us192
Pool

4 Bedroom Villa 2 Miles from Disney Entrance Kissimmee Us192

10.0 out of 10, Exceptional, (272)
"The stay was really good. The host was fantastic and communicated well. The only problem we had was ants on the kitchen counter."
4 Bedroom Villa 2 Miles from Disney Entrance Kissimmee Us192
South facing pool & spa on water conservation area in gated community
Outdoor pool, a heated pool

South facing pool & spa on water conservation area in gated community

10.0 out of 10, Exceptional, (12)
"Excellent property. Well-maintained house with plenty of space. Will definitely recommend this location to friends and family. "
South facing pool & spa on water conservation area in gated community
Luxury 7 bedroom Villa on the gated Bellavida Resort, close to everything Disney
Outdoor pool, a heated pool

Luxury 7 bedroom Villa on the gated Bellavida Resort, close to everything Disney

2.0 star property
8.0 out of 10, Very Good, (7)
"Overall good stay. Would recommend "
Luxury 7 bedroom Villa on the gated Bellavida Resort, close to everything Disney
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Winter Garden

Vacation Village at Parkway
Aerial view

Vacation Village at Parkway

3.0 star property
8.4 out of 10, Very Good, (1612)
"Excellent property "
The price is SAR 313
SAR 411 total
includes taxes & fees
16 Mar - 17 Mar
Vacation Village at Parkway
Lake Buena Vista Resort Village & Spa
2 outdoor pools, a heated pool, open 8:00 AM to 10:00 PM, pool umbrellas

Lake Buena Vista Resort Village & Spa

4.0 star property
8.4 out of 10, Very Good, (8384)
"The staff was friendly and the property was very clean. The furniture in the rooms was a bit outdated. Shower pressure was low and the hot water ran out quickly "
Lake Buena Vista Resort Village & Spa
Margaritaville Resort Orlando Cottages by Rentyl
Interior

Margaritaville Resort Orlando Cottages by Rentyl

4.0 star property
8.8 out of 10, Excellent, (1226)
"Ok"
Margaritaville Resort Orlando Cottages by Rentyl
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much do villas in Winter Garden cost?
Villas in Winter Garden cost between and per night. These stays offer the privacy to enjoy your own space at a price that’s gentle to your wallet. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Why book your villa in Winter Garden with Expedia?
With Expedia, it’s easy to find your ideal villa in Winter Garden. Traveling with the kids? Use our helpful filters to search for stays with amenities like a pool and WiFi. If you have a budget, choose how much you’re willing to spend and your preferred star rating. We’ll help you find the right place in tune with your taste and style.
How can I find cheap villas in Winter Garden?
A great way to get cheap villas in Winter Garden is with Expedia’s convenient filter tool. Refine your search results by star rating, budget and amenities to grab awesome bargains in only a click or two.